Lithium Hydroxide → Methyl 3-cyano-4-isopropoxybenzoate

HRID 222920Notes

Reaction equation

HRID 222920 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[OH-].[Li+].[CH2:16]1[CH2:20]OC[CH2:17]1>O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:16]([CH3:20])[CH3:17])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Product 1

HCID 21956805Methyl 3-cyano-4-isopropoxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3 (0.376 mol) in THF (200 mL) and water (100 mL) was added lithium hydroxide (31.6 g, 0.752 mol) and the mixture stirred for 2 hours. The reaction mixture was filtered through a silica gel plug (the pH of the filtrate was about 7) and concentrated. The residue was dried under vacuum to give 4 (0.376 mol).

Workup

  1. filtrationThe reaction mixture was filtered through a silica gel plug (the pH of the filtrate
  2. concentrationconcentrated
  3. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-5a33d79b4cfa4e35b4a2304ceb984a2c
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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